Hydrogen Bromide → HCID 22147082, compound

HRID 1823783Notes

Reaction equation

HRID 1823783 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([O:17]C)[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[Cl:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[Cl:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 10612270HCID 10612270, compound

Product 1

HCID 22147082HCID 22147082, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-benzyl-2-chloro-6-methoxy-1H-benzoimidazole (600 mg), hydrobromic acid (48%, 11 ml) and glacial acetic acid (6 ml) was heated under reflux for 1 hour. After cooling the mixture was neutralised by addition of 10% sodium bicarbonate solution then extracted 3 times with dichloromethane (30 ml). The combined extracts were dried over magnesium sulfate and then evaporated to give 3-benzyl-2-chloro-3H-benzoimidazol-5-ol (470 mg) as a yellow solid. Mass spectrum: 259 [M+H]+ retention time=3.4 minutes.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling the mixture
  4. extractionthen extracted 3 times with dichloromethane (30 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-bf85bbdd15fa467bac1c8b7f1db9ccee
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

Loading…